4-Nitroaniline → 2-chloro-3-methyl-6-nitroQuinoline

To a solution of 4-nitroaniline (10 g, 72 mmol) in chloroform at 0° was added propionyl chloride (7 mL, 80 mol) followed by triethylamine (11.1 mL). The resulting solution was stirred for 2 h at r.t. at which time the reaction mixture was washed with aq. 2N HCl. The organic layer was dried filtered and the solvent removed under vacuum to provide a solid. A solution of phosphorous oxychloride (25 mL) and N,N-dimethylformamide (4.5 mL) was stirred at 0° for 0.15 h then the above solid was added. The resulting reaction mixture was heated at 75° for 12 h at which time the volatiles were removed under vacuum. The residue was cooled in an ice bath. To the cooled mixture was carefully added water (50 mL). The resulting solids were filtered and then washed with water. The solids were extracted with chloroform, the extracts were combined, dried, filtered and the solvent removed under vacuum to afford the product, MS: m/z 224 (MH+), which was used directly in the next step.

1. washwas washed with aq. 2N HCl
2. customThe organic layer was dried
3. filtrationfiltered
4. customthe solvent removed under vacuum
5. customto provide a solid
6. additionthe above solid was added
7. customThe resulting reaction mixture
8. temperaturewas heated at 75° for 12 h at which time the volatiles
9. customwere removed under vacuum
10. temperatureThe residue was cooled in an ice bath
11. filtrationThe resulting solids were filtered
12. washwashed with water
13. extractionThe solids were extracted with chloroform
14. customdried
15. filtrationfiltered
16. customthe solvent removed under vacuum
17. customto afford the product, MS

ORD-Eintrag

ord-5d813e8fedc748868d00c8e9808dda4f

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07084156B2